Water → 5-Phenyl-3-isoxazolecarboxylic acid

HRID 1178130Notes

Reaction equation

HRID 1178130 reaction equation
O[Li].O.C[O:5][C:6]([C:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:10][N:9]=1)=[O:7].C1COCC1.O>CO>[C:13]1([C:11]2[O:10][N:9]=[C:8]([C:6]([OH:7])=[O:5])[CH:12]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 905953Methyl 5-phenyl-1,2-oxazole-3-carboxylate

Product 1

HCID 1519165-Phenyl-3-isoxazolecarboxylic acidYield 84.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

LiOH.H2O (870 mg, 20.73 mmol) was added to a solution of 5-phenyl-isoxazole-3-carboxylic acid methyl ester (2.8 g, 13.79 mmol) in a mixture of methanol (10 mL), THF (10 mL) and H2O (10 mL). The resulting reaction mixture was stirred for two and half hours at room temperature. The volatiles were then removed and the residue was diluted with water, washed with diethyl ether, acidified with con. HCl and extracted with ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated under reduced pressure to afford 5-phenyl-isoxazole-3-carboxylic acid in 84.6% yield. LC-MS purity: 96.4%.

Workup

  1. customThe resulting reaction mixture
  2. customThe volatiles were then removed
  3. additionthe residue was diluted with water
  4. washwashed with diethyl ether
  5. extractionHCl and extracted with ethyl acetate
  6. washThe organic layer was washed with brine solution
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ec42fe1ee24b488793285b289ce94648
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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